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Yours Most Sincerely

Love Letters from the Good Life

Holidays / October 20, 2026

A *Very* Late Derby Weekend Wrap-Up

I’ve mentioned before- in person, during morning affirmations, and on these pages- that the last year has been one for change. It seemed appropriate, then, that my favorite holiday season came with some shifts, as well. Whether new restaurants were visited, new events attended, or new traditions beginning to be forged, this year was the year to start.

This year, events were kept to the weekend, with Thursday’s Thurby at the track kicking us off. My handsome date and I gathered a few friends, bought a box, and gathered for breakfast juleps and bourbon balls at home before heading to Churchill Downs for the day. I’ve been so pleased with the renovations at Churchill in the areas surrounding the paddock, and for the last couple of seasons, have absolutely loved the giant, 3rd floor patio overlooking the space. Our box was adjacent, so we were able to zip out of the shade and into the sun throughout the day.

That night, 4 of us made our way to the Pine Room for fried chicken, more juleps, and cherry pie. The Pine Room is one of my favorite restaurants, period, but on Derby week, it feels as if there’s nowhere more appropriate to celebrate something so quintessentially Kentucky.

Friday, we decided to make our way to Clayton & Crume for their annual Oaks Day Brunch. This was an event I hadn’t been to before, but the photos from years past as well as my blooming friendship with the crew at C&C made this into something I didn’t want to pass. The morning was hosted at the Louisville location, where the second floor of the store (Muhammad Ali’s old gym- talk about a city that loves its history!) was transformed into a fabulous garden party scene. Fresh flowers, live music, and open bars surrounded long tables where friends of Clayton & Crume and a surprising number of out of town guests gathered round. Brunch was provided by Wiltshire Pantry, and the meal itself was one I won’t soon forget- a fresh Spring salad and savory bread pudding with chicken confit. See a clip of this event via Instagram here (and see a little glimpse of your girl in the first second!).

After toasting the season with 150 of our newest, closest friends, we made our way downtown to my friend Kokin’s pop-up shop at the Seelbach. Each year, a visit to his store makes me start planning outfits for the next season. We then made our way briefly, to Louisville Stoneware, where I was presented with a Derby present- my first ever- which was funny, considering I’d also bought him one as well… chalk that up to “new traditions.”

That night, after a quick call to a friend and former colleague in Lexington, my handsome date surprised me with a little cross-state field trip to dinner at Dudley’s on Short. While dinner (and the company!) was wonderful, the drive past Kentucky’s horse farms on such a special weekend was really something.

Derby day, we awake early to meet at a friend’s house and road trip east once again. A traditional morning tour at Four Roses started our day before we drove into Midway for pimento cheese sandwiches at Wallace Station, a little shopping along Main Street, and a pitstop for roadside ice cream from Crank and Boom. Afterwards, we made our way into Versailles for a julep class at Woodford Reserve. Class was just the four of us and our bartender, and we chatted for well over an hour while putting together both the traditional cocktail as well as a mint chocolate version.

After getting back home at 5ish, we joked about how old we’d become. At one point, I remember three days at the track, followed by staying out until the wee hours of morning, then waking up to do it all again the next day (I very distinctly remember falling asleep for the “night” while watching the sun rise the Sunday after Derby 2009). It was all we could do this year to rally and make it to dinner at the Pine Room once again, before sleeping in *very* late on Sunday morning.

The thing is, though, every year, it feels like celebrating is such a huge ordeal, and a little much, but the truth is, I wouldn’t have it any other way.

** this post is not sponsored in any way. all thoughts and opinions are my own **

** terrible iPhone photos are all my own **


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